Surprising selectivity in the transformation of dimethoxy azaindoles

Autor: Dedong Wu, Kirsten D. Gesenberg, Prashant P. Deshpande, Nachimuthu Soundararajan, John Castoro, Feng Xu, Qi Gao, Andrew J. Staab, Annie Pullockaran, Charles Pathirana
Rok vydání: 2007
Předmět:
Zdroj: Tetrahedron Letters. 48:2675-2677
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2007.02.076
Popis: Transformation of 4,7-dimethoxy-6-azaindole into 4-hydroxy-7-methoxy-6-azaindole or 7-hydroxy-4-methoxy-6-azaindole can be readily controlled by careful selection of a reagent. Treatment with concentrated HCl results in hydrolysis at the 4-position exclusively, while TMS-I provides demethylation at the 7-position only. Products were unambiguously identified by single crystal X-ray crystallography.
Databáze: OpenAIRE